diff --git a/federation/outbound.py b/federation/outbound.py
index e72d17a..53e450b 100644
--- a/federation/outbound.py
+++ b/federation/outbound.py
@@ -1,3 +1,4 @@
+import json
 import logging
 
 from federation.entities.diaspora.mappers import get_outbound_entity
@@ -70,11 +71,16 @@ def handle_send(entity, author_user, recipients=None, parent_user=None):
         public_key = recipient[1] if isinstance(recipient, tuple) and len(recipient) > 1 else None
         if public_key:
             # Private payload
-            payload = handle_create_payload(entity, author_user, to_user_key=public_key, parent_user=parent_user)
+            try:
+                payload = handle_create_payload(entity, author_user, to_user_key=public_key, parent_user=parent_user)
+                payload = json.dumps(payload)
+            except Exception as ex:
+                logger.error("handle_send - failed to generate private payload for %s: %s", id, ex)
+                continue
             # TODO get_private_endpoint should be imported per protocol
             url = get_private_endpoint(id)
             payloads.append({
-                "urls": {url}, "payload": payload,
+                "urls": {url}, "payload": payload, "content_type": "application/json",
             })
         else:
             if not public_payloads["diaspora"]["payload"]:
@@ -89,6 +95,7 @@ def handle_send(entity, author_user, recipients=None, parent_user=None):
     if public_payloads["diaspora"]["payload"]:
         payloads.append({
             "urls": public_payloads["diaspora"]["urls"], "payload": public_payloads["diaspora"]["payload"],
+            "content_type": "application/magic-envelope+xml",
         })
 
     logger.debug("handle_send - %s", payloads)
@@ -96,5 +103,7 @@ def handle_send(entity, author_user, recipients=None, parent_user=None):
     # Do actual sending
     for payload in payloads:
         for url in payload["urls"]:
-            # TODO set content type per protocol above when collecting and use here
-            send_document(url, payload["payload"])
+            try:
+                send_document(url, payload["payload"], headers={"Content-Type": payload["content_type"]})
+            except Exception as ex:
+                logger.error("handle_send - failed to send payload to %s: %s, payload: %s", url, ex, payload["payload"])
diff --git a/federation/protocols/diaspora/encrypted.py b/federation/protocols/diaspora/encrypted.py
index b7f7102..a7006e4 100644
--- a/federation/protocols/diaspora/encrypted.py
+++ b/federation/protocols/diaspora/encrypted.py
@@ -83,6 +83,6 @@ class EncryptedPayload:
         padded_payload = pkcs7_pad(payload.encode("utf-8"), AES.block_size)
         encrypted_me = b64encode(encrypter.encrypt(padded_payload))
         return {
-            "aes_key": aes_key,
-            "encrypted_magic_envelope": encrypted_me,
+            "aes_key": aes_key.decode("utf-8"),
+            "encrypted_magic_envelope": encrypted_me.decode("utf8"),
         }
diff --git a/federation/tests/test_outbound.py b/federation/tests/test_outbound.py
index d2f7bfc..e16e006 100644
--- a/federation/tests/test_outbound.py
+++ b/federation/tests/test_outbound.py
@@ -60,16 +60,18 @@ class TestHandleSend:
         handle_send(diasporapost, mock_author, recipients)
 
         # Ensure first call is a private payload
-        assert mock_send.call_args_list[0][0][0] == "https://127.0.0.1/receive/users/xyz"
-        encrypted = mock_send.call_args_list[0][0][1]
-        assert "aes_key" in encrypted
-        assert "encrypted_magic_envelope" in encrypted
+        args, kwargs = mock_send.call_args_list[0]
+        assert args[0] == "https://127.0.0.1/receive/users/xyz"
+        assert "aes_key" in args[1]
+        assert "encrypted_magic_envelope" in args[1]
+        assert kwargs['headers'] == {'Content-Type': 'application/json'}
 
         # Ensure public payloads and recipients, one per unique host
-        public_endpoints = {
-            mock_send.call_args_list[1][0][0],
-            mock_send.call_args_list[2][0][0],
-        }
+        args1, kwargs1 = mock_send.call_args_list[1]
+        args2, kwargs2 = mock_send.call_args_list[2]
+        public_endpoints = {args1[0], args2[0]}
         assert public_endpoints == {"https://example.net/receive/public", "https://localhost/receive/public"}
-        assert mock_send.call_args_list[1][0][1].startswith("<me:env xmlns:me=")
-        assert mock_send.call_args_list[2][0][1].startswith("<me:env xmlns:me=")
+        assert args1[1].startswith("<me:env xmlns:me=")
+        assert args2[1].startswith("<me:env xmlns:me=")
+        assert kwargs1['headers'] == {'Content-Type': 'application/magic-envelope+xml'}
+        assert kwargs2['headers'] == {'Content-Type': 'application/magic-envelope+xml'}